42nd Annual GRAMMY Awards
February 23, 2000
Staples Center, Los Angeles
Eligibility Year: Oct. 1, 1998, Through Sept. 30, 1999

The first GRAMMY Awards ceremony held during the 21st century is perhaps best remembered as a supernaturally smooth evening for Carlos Santana. Remarkably, the veteran guitar great and bandleader had previously won only one GRAMMY — under his own name at the 31st Annual GRAMMY Awards for Best Rock Instrumental Performance (Orchestra, Group Or Soloist) for “Blues For Salvador.” At the 42nd Annual GRAMMY Awards at Los Angeles’ Staples Center, Santana made up for lost time, winning eight awards: Record Of The Year, Album Of The Year, Best Pop Performance By A Duo Or Group With Vocals, Best Pop Collaboration With Vocals, Best Pop Instrumental Performance, Best Rock Performance By A Duo Or Group With Vocal, Best Rock Instrumental Performance and Best Rock Album. As if that wasn’t all quite enough, Santana’s “Smooth” vocal guest Rob Thomas and Itaal Shur — who wrote the song together — took home the GRAMMY for Song Of The Year.

When Bob Dylan and Lauryn Hill presented the GRAMMY for Album Of The Year for Supernatural at the end of the night, Carlos Santana spoke up for “love, understanding and oneness.” But it was one of Supernatural’s producers — and longtime Santana friend and mentor — Clive Davis who summed things up beautifully. “You’re an inspiration to every young musician throughout the globe,” Davis said of Santana. “Because when they break in they don’t know how long a career can not only last, but how long it can soar.” On this night, there could be no question that Santana was soaring.

Also making headlines this night was Jennifer Lopez whose rather minimalist green gown was much talked about. As Lopez’s co-presenter David Duchovny quipped onstage, “This is the first time in five or six years that I’m sure that nobody is looking at me.”

Among the others the crowd at Staples was looking at: Will Smith, who opened the show, the Dixie Chicks, TLC, Kid Rock and Britney Spears, whose performance began with a little girl watching the 32nd Annual GRAMMY Awards dreaming of someday performing on the show. There was also a rousing segment dedicated to the wide world of Latin music (celebrating the launch of the first Latin GRAMMY Awards in September of 2000) with fine performances from Marc Anthony, Poncho Sanchez, Ibrahim Ferrer of Buena Vista Social Club fame and Ricky Martin, a year after his triumphant performance of “The Cup Of Life.”

But it wasn’t all good vibes, revealing dresses and cool performances at the 42nd Annual GRAMMY Awards. Despite at the time having established a reputation as “The Queen of Nice,” Rosie O’Donnell had quite a barbed turn as host this year. In particular, she took aim at Whitney Houston. The host made repeated allusions to Houston’s recent arrest for marijuana possession at a Hawaiian airport, both in her opening monologue and with this introduction to the singer’s performance of “It’s Not Right But It’s Okay”: “Our next performer is a huge fan of the doobies,” O’Donnell said. Houston surmounted the jabs with a soulful version of the song and a win for Best Female R&B Vocal Performance.

Perhaps more uplifting was the chance to watch one legendary piano man salute another. Billy Joel took the stage to honor Elton John, the recipient of a GRAMMY Legend Award. “In an age of Stratocasters and wah-wah pedals, Elton John made it cool to be a piano player,” Joel explained, before Elton John performed “Philadelphia Freedom” with a little vocal support from the Backstreet Boys. “Now he is a knight, and in the United Kingdom he should be addressed as Sir Elton, but here in the good ol’ USA his friends can still call him Sharon.”